On January 12, 2006, Corddry's wife Sandra appeared with him on
a Daily Show segment in which he discussed his obsession
with having a threesome. They welcomed their first child, daughter
Sloane Sullivan Corddry, on July 3, 2006.

Corddry also hosted the 10th annual Webby Awards ceremony on June 12,
2006.

The Daily Show with Jon
Stewart

His pieces for The Daily Show frequently included
references to Boston,
Massachusetts, which he considers to be his hometown.

He had since become one of The Daily Show's popular
correspondents, where he was well known for his cocky attitude
during interviews. Since the departure of Stephen
Colbert, who left to host his own show, The Colbert
Report, and Corddry taking over the hosting duties of "This Week in God", Corddry had the most
correspondent screen time, becoming a featured part of the show.
When he took over "This Week in God," he mentioned that he is an Episcopalian.

On February 9, 2006 Corddry hosted an episode of The Daily
Show due to the absence of Jon Stewart (jokingly because the show's
regular host was "in the shop", but in fact because of
the birth of Stewart's second child).

On August 15, 2006, Corddry said "I've got like a week and a
half left, all bets are off", and then on August 21, 2006, Stewart
remarked that Corddry's last day on The Daily Show would
be August 24, 2006. Corddry appeared throughout the week, once
filing a report from inside a toilet bowl supposedly on board an
aircraft transporting John Mark Karr, and another dressed up
in a 1970s
fashion; Stewart remarked, "It's his last week, and really,
we're trying to come up with terrible things for him to have to
do."

During that last show on August 24, Corddry aired a
self-produced tribute to his
four years on the show, going out, as Stewart said, with a "poop joke".

Stewart: That was a very fitting tribute, Rob. We're gonna
miss you on the show.

Corddry: Why thank you, Jon. But wherever I go and whatever
I do, there'll always be a part of me here.

Stewart: Wow...that's a really sweet thing to
say.

Corddry: No no no, I'm not kidding. It's in the second
floor men's room, actually. That's what you get for not giving me a
proper send off.

Stewart: You're really gonna go out on a poop
joke?

Corddry: I have to stay true to myself, Jon.

Corddry left The Daily Show to work on other projects,
including The Winner, a 2007 TV
series.[2]

On October 17, 2007, Corddry made a cameo appearance as himself
at a rehab center that Samantha Bee was filming a report in.

On June 12, 2008, Corddry appeared again as the "Senior Lipizzaner Correspondent," reporting on
Bush's trip to Slovenia.
The skit ended by him asking "You think you gonna do more
Lipizzaner stories soon, or..? Because if not, I'd love to come
home, you know? See my family--hear my wife is pregnant, so..." He
added that he'd "been gone two years, give or take." Jon made him
stay.

On March 5, 2009, Corddry appeared again, discussing his own
career since The Daily Show in parody of Mark Cooper's
descent from an executive to a janitor. It was revealed that he had
distracted Jason Jones and stolen his piece, as he had come back to
beg for his old job back. He repeatedly referred to himself as
"millions of Americans" when making self-deprecating jokes and
begging for his job back.

Other
work

Corddry starred as the main character in the Fox mid-season comedy The
Winner from March 4, 2007 until the series'
cancellation.[3] He
described the show to Stuff Magazine as "sort of like a fucked-up
Wonder
Years."